Why I Traded My 9-to-5 for the Great Outdoors

When Steve Silberberg, pictured here at Yosemite National Park, hit his 40s, he decided he wanted to leave his cubicle to become a backpacking guide. Courtesy of Steve Silberberg

Welcome to the new retirement. It’s about having the freedom to decide when and how you want to take a break from work — to rest, recharge or start a new adventure — no matter your age. In our Redefining Retirement series, you’ll learn how real people are living their lives to the fullest, and the steps they took to get there.

Today, a man from Massachusetts describes how he decided to turn his passion for hiking into a second career.

For the last 20 years of my career, I was a software programmer. I liked my work, but it was stressful. I was always working on tight deadlines, and I could feel it taking a toll on my health.

My father died when he was 54 so in my 40s, I starting thinking about how I would really want to spend the rest of my life if I only had 10 years left. I decided that I wanted to do something more meaningful.

I started to think about how much I loved my twice-yearly backpacking vacations to places like the Adirondacks or Redwood National Park. I would hike for a week with a friend, taking in beautiful wilderness that few ever get to see. By the time I returned to the office, I always felt good — I weighed less, my clothes fit better and I was stress-free.

I suspected that there was a big potential market for guided wilderness treks. People are always looking for the next fun way to get fit, push themselves and see nature — why not combine all three? So in 2005, I started to get serious about pursuing my new business venture, Fitpacking, which would provide weight-loss-focused backpacking tours.

THINKING OUTSIDE THE CUBICLE

I worked for one more year as a programmer during this transition period. That helped give me some time to set up my business and start getting the word out without having to worry too much about money. I already owned my home and car outright and didn’t buy extravagant things, so my expenses were relatively low. That meant I could continue saving to help fund the venture, which took the pressure off having to turn a profit immediately.

Starting Fitpacking hasn’t always been easy and I don’t love every aspect of it. I don’t get excited to do bookkeeping, and marketing is a constant struggle. Sometimes doubts creep in. I recently had three participants back out of a trip at the last minute that I ultimately had to cancel. But then I guided a weeklong trip in the Superstition Wilderness in Arizona with 10 people that left me exhilarated.

It’s meeting the most amazing people that keeps me motivated. We get corporate executives, business owners, professionals, teachers, nurses, lawyers, retirees and, once, a woman and her teenage grandson. Each person brings the richness of their life experience with them. And once you get people away from their daily lives, bills, family problems and stressors, they become the wide-eyed idealists they were before their lives got in the way. Even the most hard-nosed executives drop their brusque veneer in the wilderness. Backpacking is the great equalizer.

Every day is different when you’re outdoors. When I’m leading a trip, I wake up to big skies, towering mountains, thundering rivers, lush meadows and vibrant forests.

I’m making less money than I did as a programmer, but I’m much happier. I think in life, decisions shouldn’t always be about maximizing profits. There are other things that can bring meaning and fulfillment. I also realized that I don’t need all the things I thought I did when I was in the corporate world. I can live with less.

That doesn’t mean I’ll be running Fitpacking trips for the rest of my life. At some point, I expect that I won’t have the physical ability to do it. I also have other goals, like designing an app or even returning to programming someday. But right now, I’m living my dream.

Take the next step.

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